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Identification of the cannabimimetic AM-1220 and its azepane isomer (N-methylazepan-3-yl)-3-(1-naphthoyl)indole in a research chemical and several herbal mixtures

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Abstract

Recently, a large number of synthetic cannabinoids have been identified in herbal mixtures. Moreover, an even higher number of cannabimimetic compounds are currently distributed as research chemicals on a gram to kilogram scale via several online trading platforms. As this situation leads to a large number of new cannabimimetics and the occurrence of isobaric substances, the analysis of such compounds using mass spectroscopy (MS) involves the risk of incorrect assignments of mass spectra. In certain cases, this leads to considerable analytical challenges. In the majority of cases, these challenges can only be mastered by combining multiple analytical techniques. We purchased a so-called research chemical advertised as the cannabimimetic compound [(N-methylpiperidin-2-yl)methyl]-3-(1-naphthoyl)indole (AM-1220) via an Internet platform. Analysis of the microcrystalline substance using gas chromatography (GC)–MS indicated the presence of pure AM-1220. However, after further purity testing utilizing thin-layer chromatography we were surprised to see an additional spot indicating a mixture of two substances with highly similar physicochemical properties. After isolation, high-resolution mass spectroscopy (HR-MS) revealed an elemental composition of C26H26N2O for both substances, proving the presence of two isobaric substances. Moreover, GC–MS and LC-HR-MS/MS experiments indicated two naphthoylindoles featuring different heterocyclic substituents at the indole nitrogen. Nuclear magnetic resonance spectroscopy verified the presence of the highly potent cannabimimetic AM-1220 and its azepane isomer. Interestingly, only a few weeks after purchasing the powder we also detected both substances in a similar proportion in several herbal mixtures for the first time.

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Acknowledgments

We thank the EU Commission (JUST/2009/DPIP/AG/0948), the German Ministry of Health, and the City of Frankfurt (Main) for funding the project "Spice and synthetic cannabinoids". Parts of this article have been published in the members’ journal of the German Society of Toxicological and Forensic Chemistry (GTFCh) as well as in the Bulletin of TIAFT [3]. We thank Prof. Torsten Arndt (Ingelheim, Germany) as well as Dr. Dimitri Gerostamoulos and Dr. Jochen Beyer (Melbourne, Australia) for kindly lifting the copyright.

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Authors and Affiliations

  1. Institute of Forensic Medicine, University Medical Center Freiburg, Albertstr. 9, 79104, Freiburg, Germany

    Stefan Kneisel & Volker Auwärter

  2. Institute of Pharmaceutical Sciences, Albert-Ludwigs-Universität Freiburg, Albertstr. 25, 79104, Freiburg, Germany

    Philippe Bisel, Volker Brecht & Michael Müller

  3. Institute of Legal Medicine, University Hospital Charité Berlin, Turmstr. 21, 10559, Berlin, Germany

    Sebastian Broecker

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  1. Stefan Kneisel
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  2. Philippe Bisel
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  3. Volker Brecht
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  4. Sebastian Broecker
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  5. Michael Müller
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  6. Volker Auwärter
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Correspondence to Volker Auwärter.

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Kneisel, S., Bisel, P., Brecht, V. et al. Identification of the cannabimimetic AM-1220 and its azepane isomer (N-methylazepan-3-yl)-3-(1-naphthoyl)indole in a research chemical and several herbal mixtures. Forensic Toxicol 30, 126–134 (2012). https://doi.org/10.1007/s11419-012-0137-6

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